Toward the synthesis of pyroglutamate lauroyl ester: biocatalysis versus chemical catalysis

• Published in: Biotechnology letters Vol. 26; no. 3; pp. 193 - 196
• Main Authors: Villeneuve, P, Barea, B, Barouh, N, Turon, F, Figueroa-Espinoza, M, Piombo, G, Dhuique-Mayer, C, Pina, M
• Format: Journal Article
• Language: English
• Published: Dordrecht Springer 01-02-2004; Springer Nature B.V
• Subjects: biocatalysis; biocatalysts; Biological and medical sciences; Biology; Biotechnology; Candida antarctica; carboxylic ester hydrolases; Catalysis; Chemical synthesis; Chemicals; Esterification; Fundamental and applied biological sciences. Psychology; Ion exchange; ion exchange resins; Ion Exchange Resins - chemistry; Isoenzymes - chemistry; Lipase - chemistry; Pseudozyma antarctica; Pyrrolidonecarboxylic Acid - chemical synthesis; Pyrrolidonecarboxylic Acid - chemistry; Q1; Q2; Resins; Triacylglycerol lipase; Biocatalysis; Enzyme; lipase; Fatty ester; Triacylglycerol lipase; Alcohol; Esterases; Carboxylic ester hydrolases; Alcoholysis; lauroyl alcohol; Hydrolases; Catalysis; Ion exchange resin; pyroglutamic fatty ester; Comparative study
• ISSN: 0141-5492; 1573-6776
• DOI: 10.1023/B:BILE.0000013710.46900.10

The synthesis of dodecyl pyroglutamate (or pyroglutamate lauroyl ester) was achieved in a two-step process involving a pyroglutamic acid alkyl ester intermediate. The reaction was carried out either by lipase or by chemical catalysis using ion exchange resin. Among the various tested lipases, the one from Candida antarctica B gave the best results allowing 73% formation of the desired ester after 6 h. Comparing the efficiency of this latter lipase with the one of Amberlyst IR120H resin in catalyzing this reaction, the biocatalyst gave a molar yield of pyroglutamate lauroyl ester of 79% compared to 69% when using the ion exchange resin starting with 1.04 mmol substrate in each case.